Vacation rentals in Looe Key

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Looe Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A cozy seating area is positioned by large windows, allowing views of lush greenery outside. A light sofa is complemented by decorative pillows, while a modern chair alongside a small table adds to the tranquil setting.

Loft in Miami

4.9 out of 5 average rating, 268 reviews

The Garage. Charming loft. Self check-in. Parking.

Charming & differentiated NorthCoconut Grove loft/studio. Immersed in the green, which you will enjoy in the private patio. Recently renovated, with all the amenities and top-end appliances. Ideal for 2. Sleeps up to 4 (Queen bed + sofa bed). Easy, quick access to I-95, MIA Airport, Coral Gables, Brickell, Wynwood & Downtow. Free parking in front of the unit. Close to the Metro Rail Pets are welcome! Please inform us when you book. Additional fee is $100 per stay per pet. — No smoking allowed

Guest favorite

A clear view of the waterfront features a well-maintained seawall alongside tranquil blue waters. Palm trees line the shore, offering a tropical feel. The space is enhanced by direct access for boating activities, emphasizing the serene and inviting coastal environment.

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Guest favorite

An open living area features large windows providing a 270-degree view of the waterfront. A white sofa and stylish chairs are arranged, complemented by a sleek dining area. Natural light floods the space, highlighting modern furnishings and the serene blue ocean.

Apartment in Old Havana

4.96 out of 5 average rating, 384 reviews

Sea View Loft Suite 270°, Free Wifi Internet

The extraordinary 270° Sea-view Penthouse Suite is located in the heart of the historical old town of Havana at the end of the well known boulevard Obispo (Bayside) and the famous Park "Plaza de Armas" just next to the traditional luxury Hotel Santa Isabel. Check out also the New door to door double unit as a special offer https://www.airbnb.de/rooms/37442714?adults=1&guests=1&s=13&unique_share_id=32d11d71-7b60-49d9-9472-adbbd5 You will get a impression of authentic cuban living and lifestyle.

Guest favorite

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

4.96 out of 5 average rating, 111 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Guest favorite

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

Condo in Key Colony Beach

4.91 out of 5 average rating, 192 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Top guest favorite

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 115 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Superhost

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

Cottage in Little Torch Key

4.88 out of 5 average rating, 171 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Guest favorite

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

4.95 out of 5 average rating, 130 reviews

Amazing houseboat with a sunset eco-trip included

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Top guest favorite

An aerial view showcases a waterfront property at night, featuring a softly illuminated pool adjacent to the house. Green lights reflect in the water, highlighting the dock and surrounding greenery. The property is framed by a serene landscape, emphasizing its tranquil atmosphere.

Home in Miami

5 out of 5 average rating, 53 reviews

Waterfront Miami Oasis w/ Kayaks | Heated Pool

Escape to a unique Miami waterfront retreat where you can kayak from the backyard, unwind in a hot tub, and swim in a pristine Heated Pool. This quiet family-friendly haven offers a chance to spot local wildlife like ducks and tropical birds. Experience a trendy vibe, featuring a mini golf course, cornhole, pool table, multicade play system and so much more. With a clean, spacious interior and a central location near both Miami and Aventura, it’s perfect for a memorable getaway.

Guest favorite

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

Home in Cudjoe Key

4.86 out of 5 average rating, 107 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Top guest favorite

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

Condo in Key West

4.97 out of 5 average rating, 106 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Guest favorite

A waterfront patio features comfortable wicker seating overlooking serene water. The setting sun casts a warm glow, illuminating the scene with subtle light. Colorful decorations hang from the thatched roof, complementing the tranquil atmosphere while boats are visible in the distance.

Home in Key Largo

4.93 out of 5 average rating, 121 reviews

The Paradise 2

Relax with the whole family at this peaceful place to stay. Our home is located right by the water. Modern spacious and spotless with private parking, fast Wi-Fi, cold AC plus cozy beds and pillows in every bed. Relax on the waterfront patio chairs, swim in our newly renovated pool, watch the manatees and dolphins swim by and go fishing from our backyard dock anytime. We are sure you will absolutely love our Tiny Home!